# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_t
_audit_block_doi                 10.5517/ccdc.csd.cc20txmd
_database_code_depnum_ccdc_archive 'CCDC 1871954'
_audit_update_record             
;
2018-10-06 deposited with the CCDC.
2018-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H22 N O2 P'
_chemical_formula_sum            'C27 H22 N O2 P'
_chemical_formula_weight         423.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.8836(5)
_cell_length_b                   12.2399(8)
_cell_length_c                   11.1988(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.174(2)
_cell_angle_gamma                90
_cell_volume                     1080.62(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4228
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.41

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4503
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.584
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_point_group_measured_fraction_full 0.817
_reflns_number_total             3118
_reflns_number_gt                3059
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.568
_reflns_Friedel_fraction_max     0.624
_reflns_Friedel_fraction_full    0.624

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+0.1974P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3118
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4872(3) 1.2214(2) 0.8472(2) 0.0209(5) Uani 1 1 d . . . . .
C2 C 0.3416(4) 1.2165(3) 0.9161(3) 0.0446(9) Uani 1 1 d . . . . .
H2A H 0.277678 1.150819 0.919704 0.054 Uiso 1 1 calc R U . . .
C3 C 0.2892(4) 1.3075(3) 0.9798(3) 0.0515(10) Uani 1 1 d . . . . .
H3A H 0.189007 1.303730 1.026571 0.062 Uiso 1 1 calc R U . . .
C4 C 0.3799(3) 1.4024(2) 0.9762(2) 0.0293(6) Uani 1 1 d . . . . .
H4A H 0.343450 1.464268 1.020495 0.035 Uiso 1 1 calc R U . . .
C5 C 0.5241(3) 1.4079(2) 0.9081(2) 0.0278(6) Uani 1 1 d . . . . .
H5A H 0.587678 1.473744 0.905147 0.033 Uiso 1 1 calc R U . . .
C6 C 0.5771(3) 1.3178(2) 0.8437(2) 0.0262(6) Uani 1 1 d . . . . .
H6A H 0.676732 1.322461 0.796470 0.031 Uiso 1 1 calc R U . . .
C7 C 0.5552(3) 1.1243(2) 0.7817(2) 0.0204(5) Uani 1 1 d . . . . .
C8 C 0.4962(3) 0.9385(2) 0.7244(2) 0.0196(5) Uani 1 1 d . . . . .
H8A H 0.611982 0.931187 0.702552 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3958(3) 0.8519(2) 0.70531(18) 0.0187(5) Uani 1 1 d . . . . .
C10 C 0.4707(3) 0.7534(2) 0.6481(2) 0.0195(5) Uani 1 1 d . . . . .
C11 C 0.4548(3) 0.6488(2) 0.6957(2) 0.0230(5) Uani 1 1 d . . . . .
H11A H 0.390846 0.638140 0.766485 0.028 Uiso 1 1 calc R U . . .
C12 C 0.5311(3) 0.5602(2) 0.6408(2) 0.0263(6) Uani 1 1 d . . . . .
H12A H 0.517820 0.489146 0.673510 0.032 Uiso 1 1 calc R U . . .
C13 C 0.6267(3) 0.5746(2) 0.5386(2) 0.0280(6) Uani 1 1 d . . . . .
H13A H 0.680276 0.513734 0.501911 0.034 Uiso 1 1 calc R U . . .
C14 C 0.6437(3) 0.6775(2) 0.4902(2) 0.0281(6) Uani 1 1 d . . . . .
H14A H 0.709605 0.687687 0.420165 0.034 Uiso 1 1 calc R U . . .
C15 C 0.5651(3) 0.7661(2) 0.5433(2) 0.0231(5) Uani 1 1 d . . . . .
H15A H 0.575369 0.836449 0.508227 0.028 Uiso 1 1 calc R U . . .
C16 C 0.0704(3) 0.8696(2) 0.58701(19) 0.0192(5) Uani 1 1 d . . . . .
C17 C -0.0440(3) 0.9543(2) 0.5673(2) 0.0251(6) Uani 1 1 d . . . . .
H17A H -0.068603 1.004751 0.629337 0.030 Uiso 1 1 calc R U . . .
C18 C -0.1220(3) 0.9649(3) 0.4567(3) 0.0330(7) Uani 1 1 d . . . . .
H18A H -0.199832 1.022889 0.443308 0.040 Uiso 1 1 calc R U . . .
C19 C -0.0874(3) 0.8918(3) 0.3659(2) 0.0337(7) Uani 1 1 d . . . . .
H19A H -0.141533 0.899589 0.290464 0.040 Uiso 1 1 calc R U . . .
C20 C 0.0266(3) 0.8070(3) 0.3851(2) 0.0282(6) Uani 1 1 d . . . . .
H20A H 0.050293 0.756686 0.322732 0.034 Uiso 1 1 calc R U . . .
C21 C 0.1055(3) 0.7957(2) 0.4949(2) 0.0221(5) Uani 1 1 d . . . . .
H21A H 0.183607 0.737702 0.507863 0.027 Uiso 1 1 calc R U . . .
C22 C 0.0946(3) 0.7423(2) 0.8056(2) 0.0200(5) Uani 1 1 d . . . . .
C23 C 0.1502(3) 0.7249(2) 0.9227(2) 0.0255(6) Uani 1 1 d . . . . .
H23A H 0.229443 0.773677 0.957985 0.031 Uiso 1 1 calc R U . . .
C24 C 0.0904(3) 0.6372(2) 0.9871(2) 0.0286(6) Uani 1 1 d . . . . .
H24A H 0.127198 0.626243 1.067081 0.034 Uiso 1 1 calc R U . . .
C25 C -0.0231(3) 0.5649(2) 0.9354(2) 0.0273(6) Uani 1 1 d . . . . .
H25A H -0.062970 0.503799 0.979526 0.033 Uiso 1 1 calc R U . . .
C26 C -0.0786(3) 0.5815(2) 0.8196(2) 0.0262(6) Uani 1 1 d . . . . .
H26A H -0.156430 0.531714 0.784266 0.031 Uiso 1 1 calc R U . . .
C27 C -0.0209(3) 0.6708(2) 0.7548(2) 0.0221(6) Uani 1 1 d . . . . .
H27A H -0.060755 0.682734 0.675762 0.027 Uiso 1 1 calc R U . . .
P1 P 0.16989(7) 0.86376(5) 0.73209(5) 0.01846(16) Uani 1 1 d . . . . .
N1 N 0.4477(3) 1.03729(17) 0.77252(17) 0.0198(4) Uani 1 1 d . . . . .
H1A H 0.343017 1.044542 0.798461 0.024 Uiso 1 1 calc R U . . .
O1 O 0.6987(2) 1.12317(16) 0.74086(16) 0.0285(4) Uani 1 1 d . . . . .
O2 O 0.1313(2) 0.96343(15) 0.80426(16) 0.0265(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.377(4) . ?
C1 C2 1.386(4) . ?
C1 C7 1.497(3) . ?
C2 C3 1.386(4) . ?
C3 C4 1.365(4) . ?
C4 C5 1.373(4) . ?
C5 C6 1.383(4) . ?
C7 O1 1.221(3) . ?
C7 N1 1.365(3) . ?
C8 C9 1.340(4) . ?
C8 N1 1.378(3) . ?
C9 C10 1.488(3) . ?
C9 P1 1.812(2) . ?
C10 C11 1.392(4) . ?
C10 C15 1.400(3) . ?
C11 C12 1.386(4) . ?
C12 C13 1.383(4) . ?
C13 C14 1.379(4) . ?
C14 C15 1.384(4) . ?
C16 C17 1.392(4) . ?
C16 C21 1.400(3) . ?
C16 P1 1.803(2) . ?
C17 C18 1.386(4) . ?
C18 C19 1.382(4) . ?
C19 C20 1.390(4) . ?
C20 C21 1.384(3) . ?
C22 C27 1.384(4) . ?
C22 C23 1.398(3) . ?
C22 P1 1.800(3) . ?
C23 C24 1.377(4) . ?
C24 C25 1.384(4) . ?
C25 C26 1.382(4) . ?
C26 C27 1.389(4) . ?
P1 O2 1.4951(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.7(2) . . ?
C6 C1 C7 118.7(2) . . ?
C2 C1 C7 122.5(2) . . ?
C3 C2 C1 120.0(3) . . ?
C4 C3 C2 120.8(3) . . ?
C3 C4 C5 119.5(3) . . ?
C4 C5 C6 120.2(3) . . ?
C1 C6 C5 120.8(2) . . ?
O1 C7 N1 122.6(2) . . ?
O1 C7 C1 121.8(2) . . ?
N1 C7 C1 115.6(2) . . ?
C9 C8 N1 126.3(2) . . ?
C8 C9 C10 118.3(2) . . ?
C8 C9 P1 119.39(19) . . ?
C10 C9 P1 121.84(18) . . ?
C11 C10 C15 118.1(2) . . ?
C11 C10 C9 122.9(2) . . ?
C15 C10 C9 118.9(2) . . ?
C12 C11 C10 120.7(2) . . ?
C13 C12 C11 120.4(3) . . ?
C14 C13 C12 119.7(3) . . ?
C13 C14 C15 120.2(2) . . ?
C14 C15 C10 120.9(2) . . ?
C17 C16 C21 119.6(2) . . ?
C17 C16 P1 116.90(19) . . ?
C21 C16 P1 123.48(19) . . ?
C18 C17 C16 119.8(3) . . ?
C17 C18 C19 120.6(3) . . ?
C18 C19 C20 119.9(2) . . ?
C21 C20 C19 120.1(3) . . ?
C20 C21 C16 120.0(2) . . ?
C27 C22 C23 119.5(2) . . ?
C27 C22 P1 123.51(19) . . ?
C23 C22 P1 116.9(2) . . ?
C24 C23 C22 120.3(2) . . ?
C23 C24 C25 120.1(2) . . ?
C26 C25 C24 120.1(2) . . ?
C25 C26 C27 120.2(2) . . ?
C22 C27 C26 120.0(2) . . ?
O2 P1 C22 111.02(10) . . ?
O2 P1 C16 111.48(12) . . ?
C22 P1 C16 107.54(12) . . ?
O2 P1 C9 110.86(11) . . ?
C22 P1 C9 109.57(12) . . ?
C16 P1 C9 106.18(9) . . ?
C7 N1 C8 122.7(2) . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.038



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_zdl3_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1537789'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2018-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H22 N O2 P'
_chemical_formula_sum            ' C27 H22 N O2 P'
_chemical_formula_weight         423.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.0253(6)
_cell_length_b                   9.0011(9)
_cell_length_c                   10.3679(11)
_cell_angle_alpha                75.005(3)
_cell_angle_beta                 76.437(3)
_cell_angle_gamma                89.090(3)
_cell_volume                     527.40(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4758
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.27

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             222
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.155
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8754
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.345
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             5236
_reflns_number_gt                4703
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.953
_reflns_Friedel_fraction_max     0.948
_reflns_Friedel_fraction_full    0.974

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0303P)²+0.1175P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5091
_refine_ls_number_parameters     280
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.16769(10) 0.51336(8) 0.38967(7) 0.01250(16) Uani 1 1 d . . . . .
N1 N 0.5271(4) 0.4059(3) 0.6825(3) 0.0161(5) Uani 1 1 d . . . . .
H1 H 0.5171 0.4872 0.7154 0.019 Uiso 1 1 calc R U . . .
O1 O 0.6568(4) 0.1666(2) 0.7007(2) 0.0224(5) Uani 1 1 d . . . . .
C1 C 0.7784(5) 0.3123(3) 0.8352(3) 0.0151(6) Uani 1 1 d . . . . .
O2 O -0.0804(3) 0.5438(2) 0.4220(2) 0.0189(5) Uani 1 1 d . . . . .
C2 C 0.9434(5) 0.2084(4) 0.8671(3) 0.0198(6) Uani 1 1 d . . . . .
H2 H 0.9654 0.1228 0.8284 0.024 Uiso 1 1 calc R U . . .
C3 C 1.0755(5) 0.2281(4) 0.9540(3) 0.0239(7) Uani 1 1 d . . . . .
H3 H 1.1883 0.1569 0.9746 0.029 Uiso 1 1 calc R U . . .
C4 C 1.0430(6) 0.3522(4) 1.0112(3) 0.0252(7) Uani 1 1 d . . . . .
H4 H 1.1352 0.3668 1.0701 0.030 Uiso 1 1 calc R U . . .
C5 C 0.8774(6) 0.4545(4) 0.9828(3) 0.0266(7) Uani 1 1 d . . . . .
H5 H 0.8544 0.5386 1.0233 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7445(5) 0.4353(4) 0.8956(3) 0.0213(7) Uani 1 1 d . . . . .
H6 H 0.6300 0.5059 0.8768 0.026 Uiso 1 1 calc R U . . .
C7 C 0.6497(5) 0.2866(3) 0.7353(3) 0.0148(6) Uani 1 1 d . . . . .
C8 C 0.4176(5) 0.4048(3) 0.5793(3) 0.0153(6) Uani 1 1 d . . . . .
H8 H 0.4198 0.3141 0.5483 0.018 Uiso 1 1 calc R U . . .
C9 C 0.3082(5) 0.5257(3) 0.5208(3) 0.0144(6) Uani 1 1 d . . . . .
C10 C 0.2983(5) 0.6729(3) 0.5618(3) 0.0139(6) Uani 1 1 d . . . . .
C11 C 0.4985(5) 0.7595(3) 0.5466(3) 0.0167(6) Uani 1 1 d . . . . .
H11 H 0.6423 0.7258 0.5068 0.020 Uiso 1 1 calc R U . . .
C12 C 0.4886(5) 0.8932(3) 0.5891(3) 0.0180(6) Uani 1 1 d . . . . .
H12 H 0.6258 0.9500 0.5793 0.022 Uiso 1 1 calc R U . . .
C13 C 0.2803(5) 0.9451(4) 0.6458(3) 0.0195(6) Uani 1 1 d . . . . .
H13 H 0.2741 1.0374 0.6745 0.023 Uiso 1 1 calc R U . . .
C14 C 0.0809(5) 0.8614(4) 0.6603(3) 0.0213(7) Uani 1 1 d . . . . .
H14 H -0.0625 0.8969 0.6987 0.026 Uiso 1 1 calc R U . . .
C15 C 0.0888(5) 0.7264(3) 0.6191(3) 0.0185(6) Uani 1 1 d . . . . .
H15 H -0.0490 0.6697 0.6300 0.022 Uiso 1 1 calc R U . . .
C16 C 0.3214(5) 0.6496(3) 0.2343(3) 0.0148(6) Uani 1 1 d . . . . .
C17 C 0.5429(5) 0.7082(3) 0.2130(3) 0.0183(6) Uani 1 1 d . . . . .
H17 H 0.6252 0.6764 0.2825 0.022 Uiso 1 1 calc R U . . .
C18 C 0.6430(6) 0.8136(4) 0.0898(3) 0.0237(7) Uani 1 1 d . . . . .
H18 H 0.7935 0.8549 0.0760 0.028 Uiso 1 1 calc R U . . .
C19 C 0.5274(6) 0.8593(4) -0.0128(3) 0.0247(7) Uani 1 1 d . . . . .
H19 H 0.5976 0.9317 -0.0966 0.030 Uiso 1 1 calc R U . . .
C20 C 0.3079(6) 0.7989(4) 0.0071(3) 0.0277(7) Uani 1 1 d . . . . .
H20 H 0.2284 0.8281 -0.0640 0.033 Uiso 1 1 calc R U . . .
C21 C 0.2050(5) 0.6959(4) 0.1309(3) 0.0214(7) Uani 1 1 d . . . . .
H21 H 0.0533 0.6566 0.1451 0.026 Uiso 1 1 calc R U . . .
C22 C 0.2167(5) 0.3290(3) 0.3527(3) 0.0142(6) Uani 1 1 d . . . . .
C23 C 0.0281(5) 0.2270(3) 0.3813(3) 0.0184(6) Uani 1 1 d . . . . .
H23 H -0.1181 0.2513 0.4274 0.022 Uiso 1 1 calc R U . . .
C24 C 0.4304(5) 0.2915(4) 0.2856(3) 0.0192(6) Uani 1 1 d . . . . .
H24 H 0.5593 0.3599 0.2666 0.023 Uiso 1 1 calc R U . . .
C25 C 0.4560(5) 0.1552(4) 0.2463(3) 0.0228(7) Uani 1 1 d . . . . .
H25 H 0.6019 0.1305 0.2001 0.027 Uiso 1 1 calc R U . . .
C26 C 0.2677(6) 0.0545(4) 0.2749(3) 0.0230(7) Uani 1 1 d . . . . .
H26 H 0.2848 -0.0392 0.2482 0.028 Uiso 1 1 calc R U . . .
C27 C 0.0548(6) 0.0908(4) 0.3422(3) 0.0221(7) Uani 1 1 d . . . . .
H27 H -0.0735 0.0217 0.3617 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.491(2) . ?
P1 C9 1.788(3) . ?
P1 C22 1.802(3) . ?
P1 C16 1.808(3) . ?
N1 C7 1.364(4) . ?
N1 C8 1.384(3) . ?
N1 H1 0.8800 . ?
O1 C7 1.220(3) . ?
C1 C2 1.392(4) . ?
C1 C6 1.398(4) . ?
C1 C7 1.495(4) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.345(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.489(4) . ?
C10 C15 1.399(4) . ?
C10 C11 1.402(4) . ?
C11 C12 1.380(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.389(4) . ?
C16 C17 1.390(4) . ?
C17 C18 1.388(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C24 1.395(4) . ?
C22 C23 1.399(4) . ?
C23 C27 1.383(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.388(5) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 C9 113.98(13) . . ?
O2 P1 C22 111.77(12) . . ?
C9 P1 C22 109.07(13) . . ?
O2 P1 C16 111.42(13) . . ?
C9 P1 C16 105.99(13) . . ?
C22 P1 C16 103.99(13) . . ?
C7 N1 C8 122.9(2) . . ?
C7 N1 H1 118.5 . . ?
C8 N1 H1 118.5 . . ?
C2 C1 C6 118.8(3) . . ?
C2 C1 C7 117.5(3) . . ?
C6 C1 C7 123.7(3) . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O1 C7 N1 121.6(3) . . ?
O1 C7 C1 122.0(3) . . ?
N1 C7 C1 116.4(2) . . ?
C9 C8 N1 123.3(3) . . ?
C9 C8 H8 118.4 . . ?
N1 C8 H8 118.4 . . ?
C8 C9 C10 122.0(3) . . ?
C8 C9 P1 120.3(2) . . ?
C10 C9 P1 117.6(2) . . ?
C15 C10 C11 118.4(3) . . ?
C15 C10 C9 120.6(3) . . ?
C11 C10 C9 121.0(3) . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 119.5(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C21 C16 C17 119.3(3) . . ?
C21 C16 P1 116.0(2) . . ?
C17 C16 P1 124.7(2) . . ?
C18 C17 C16 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 121.0(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 119.6(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 119.8(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C16 120.7(3) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C24 C22 C23 119.4(3) . . ?
C24 C22 P1 122.3(2) . . ?
C23 C22 P1 118.1(2) . . ?
C27 C23 C22 119.9(3) . . ?
C27 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C22 120.5(3) . . ?
C25 C24 H24 119.7 . . ?
C22 C24 H24 119.7 . . ?
C24 C25 C26 119.8(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C27 C26 C25 120.0(3) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C23 C27 C26 120.4(3) . . ?
C23 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.6(4) . . . . ?
C7 C1 C2 C3 177.3(3) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C4 C5 C6 C1 -0.3(5) . . . . ?
C2 C1 C6 C5 1.5(4) . . . . ?
C7 C1 C6 C5 -177.3(3) . . . . ?
C8 N1 C7 O1 -5.1(4) . . . . ?
C8 N1 C7 C1 173.6(2) . . . . ?
C2 C1 C7 O1 12.7(4) . . . . ?
C6 C1 C7 O1 -168.4(3) . . . . ?
C2 C1 C7 N1 -166.0(3) . . . . ?
C6 C1 C7 N1 12.9(4) . . . . ?
C7 N1 C8 C9 -175.8(3) . . . . ?
N1 C8 C9 C10 0.7(4) . . . . ?
N1 C8 C9 P1 -179.1(2) . . . . ?
O2 P1 C9 C8 122.6(2) . . . . ?
C22 P1 C9 C8 -3.1(3) . . . . ?
C16 P1 C9 C8 -114.5(2) . . . . ?
O2 P1 C9 C10 -57.2(2) . . . . ?
C22 P1 C9 C10 177.1(2) . . . . ?
C16 P1 C9 C10 65.7(2) . . . . ?
C8 C9 C10 C15 -117.7(3) . . . . ?
P1 C9 C10 C15 62.1(3) . . . . ?
C8 C9 C10 C11 60.8(4) . . . . ?
P1 C9 C10 C11 -119.3(3) . . . . ?
C15 C10 C11 C12 0.8(4) . . . . ?
C9 C10 C11 C12 -177.8(3) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C13 C14 C15 C10 -0.3(5) . . . . ?
C11 C10 C15 C14 -0.3(4) . . . . ?
C9 C10 C15 C14 178.4(3) . . . . ?
O2 P1 C16 C21 -35.9(3) . . . . ?
C9 P1 C16 C21 -160.4(2) . . . . ?
C22 P1 C16 C21 84.6(2) . . . . ?
O2 P1 C16 C17 144.3(2) . . . . ?
C9 P1 C16 C17 19.8(3) . . . . ?
C22 P1 C16 C17 -95.1(3) . . . . ?
C21 C16 C17 C18 0.9(4) . . . . ?
P1 C16 C17 C18 -179.4(2) . . . . ?
C16 C17 C18 C19 -1.0(5) . . . . ?
C17 C18 C19 C20 -0.2(5) . . . . ?
C18 C19 C20 C21 1.4(5) . . . . ?
C19 C20 C21 C16 -1.5(5) . . . . ?
C17 C16 C21 C20 0.4(4) . . . . ?
P1 C16 C21 C20 -179.4(3) . . . . ?
O2 P1 C22 C24 162.7(2) . . . . ?
C9 P1 C22 C24 -70.3(3) . . . . ?
C16 P1 C22 C24 42.4(3) . . . . ?
O2 P1 C22 C23 -11.1(3) . . . . ?
C9 P1 C22 C23 115.8(2) . . . . ?
C16 P1 C22 C23 -131.4(2) . . . . ?
C24 C22 C23 C27 -0.3(4) . . . . ?
P1 C22 C23 C27 173.7(2) . . . . ?
C23 C22 C24 C25 0.5(4) . . . . ?
P1 C22 C24 C25 -173.3(2) . . . . ?
C22 C24 C25 C26 -0.4(5) . . . . ?
C24 C25 C26 C27 0.1(5) . . . . ?
C22 C23 C27 C26 0.0(4) . . . . ?
C25 C26 C27 C23 0.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C17 H17 O2 0.95 2.63 3.546(4) 162.7 1_655

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.050



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    ', Heat-sensitive,Light-sensitive'
